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The Work of You
This is a podcast about the leadership that matters most — the kind that starts from within.
Hosted by certified behavioral coach and Enneagram expert Jen Ostrich, The Work of You is for high-achieving humans ready to stop repeating patterns and start leading themselves differently.
Through insights from coaching, the Enneagram, and her own personal inner overhaul, Jen brings honesty, humor, and sharp emotional clarity to the table. With real talk, self-awareness tools, and a healthy dose of tough love, she helps you uncover what’s driving you, shift what’s no longer serving you, and ultimately do the work of you — one honest episode at a time.
This isn’t about fixing yourself. It’s about finally understanding yourself — so your choices, relationships, and leadership can actually align with who you truly are.
The Work of You
Living in Alignment at 50! [S2 Ep28]
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Turning 50 has a way of making you honest. On the eve of her fifth decade, Jen pulls up the very first episode she ever recorded — Living in Alignment: The First Step to Leading You — and asks herself the question she asks everyone else: am I actually living this? The answer is yes. And the story of how she got there is worth hearing again, whether for the first time or the tenth.
This episode pairs a birthday reflection with a replay of Jen's inaugural episode, built around a simple but powerful framework she sketched in a notebook during coach training at the Hudson Institute. Using a visual of six arrows — career, community, family, friends, love, and current job — she maps what it looks like to spend your twenties and thirties pointing yourself toward everything outside you, and what it takes to finally flip those arrows back in. Jen walks through her own five-year reckoning: leaving Philadelphia, losing her mom, launching a coaching practice from scratch, and landing in Austin with every arrow pointing inward. She closes the episode with concrete prompts to help you do the same inventory on your own life.
In this episode, we explore:
- The alignment framework: A visual tool Jen developed in coach training — six arrows, one for each major life system — that reveals where you're living authentically and where you're still trying to fit yourself to something outside you.
- The shock point moment: How losing her mom at 33 became the pivotal event that reshaped every aspect of Jen's life — geography, career, relationships, and sense of self — and introduced her to the concept of Post-Traumatic Growth.
- Flipping the arrows: A year-by-year account of how Jen changed her city, career, friend group, and more — and why it was the hardest, most rewarding work she's ever done.
The Work of You - Reflective Prompt:
1. Where am I living in alignment and where may I be out of alignment?
Resources | Links:
50 Layers Deep (Jen's birthday essay) — available on The Work of You Substack this week
Living in Alignment - The First Step in Leading You [S1 E1]
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